#------------------------------------------------------------------------------
#$Date: 2022-06-30 04:58:50 +0300 (Thu, 30 Jun 2022) $
#$Revision: 276425 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/26/2022627.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2022627
loop_
_publ_author_name
'Bosch, Eric'
'Bowling, Nathan P.'
_publ_section_title
;
 Co-operative halogen bonds and nonconventional
 sp-C---H···O hydrogen bonds in 1:1 cocrystals
 formed between diethynylpyridines and N-halosuccinimides
;
_journal_coeditor_code           EF3030
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622006635
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C4 H4 I N O2, C9 H5 N'
_chemical_formula_moiety         'C4 H4 I N O2, C9 H5 N'
_chemical_formula_sum            'C13 H9 I N2 O2'
_chemical_formula_weight         352.12
_chemical_name_systematic
;
3,5-Diethynylpyridine--N-iodosuccinimide (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.6060(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4088(9)
_cell_length_b                   5.3200(4)
_cell_length_c                   23.5462(19)
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      3.21
_cell_volume                     1303.35(18)
_computing_cell_refinement
;
SMART (Bruker, 2014)
;
_computing_data_collection
;
SMART (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
X-SEED (Barbour, 2020)
;
_computing_publication_material
;
X-SEED (Barbour, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3660
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-I CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15299
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.367
_diffrn_reflns_theta_min         1.730
_exptl_absorpt_coefficient_mu    2.452
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.511
_refine_diff_density_min         -0.555
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2931
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0219
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0155P)²+1.0427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0441
_refine_ls_wR_factor_ref         0.0463
_reflns_number_gt                2463
_reflns_number_total             2931
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef3030sup1.cif
_cod_data_source_block           35DEP_u008226NIS
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2022627
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I1 0.64053(2) 0.66847(3) 0.38633(2) 0.01271(6) Uani d 1 . .
O O1 0.74212(18) 1.0953(3) 0.29605(8) 0.0186(4) Uani d 1 . .
O O2 0.38818(18) 0.5912(4) 0.29871(8) 0.0216(4) Uani d 1 . .
N N2 0.57353(19) 0.8234(4) 0.30937(8) 0.0130(4) Uani d 1 . .
N N1 0.7240(2) 0.5084(4) 0.48004(8) 0.0144(5) Uani d 1 . .
C C2 0.6748(2) 0.0158(5) 0.58877(11) 0.0161(6) Uani d 1 . .
C C10 0.6389(2) 1.0113(5) 0.28076(10) 0.0131(5) Uani d 1 . .
C C4 0.6758(2) 0.3118(5) 0.50765(11) 0.0148(5) Uani d 1 . .
H H4 0.603413 0.226817 0.491411 0.018 Uiso calc 1 . .
C C11 0.5590(3) 1.0849(5) 0.22881(11) 0.0162(6) Uani d 1 . .
H H11A 0.605320 1.046894 0.193663 0.019 Uiso calc 1 . .
H H11B 0.538554 1.266611 0.229472 0.019 Uiso calc 1 . .
C C6 0.8830(2) 0.5613(5) 0.55450(11) 0.0138(5) Uani d 1 . .
C C5 0.8254(2) 0.6301(5) 0.50297(11) 0.0141(5) Uani d 1 . .
H H5 0.859321 0.769463 0.483115 0.017 Uiso calc 1 . .
C C7 0.8337(2) 0.3556(5) 0.58288(10) 0.0140(5) Uani d 1 . .
H H7 0.871685 0.302664 0.618033 0.017 Uiso calc 1 . .
C C3 0.7278(3) 0.2267(5) 0.55945(11) 0.0144(5) Uani d 1 . .
C C1 0.6360(3) -0.1574(6) 0.61448(12) 0.0194(6) Uani d 1 . .
C C12 0.4365(3) 0.9272(5) 0.23197(11) 0.0188(6) Uani d 1 . .
H H12A 0.360566 1.036019 0.237203 0.023 Uiso calc 1 . .
H H12B 0.422869 0.826974 0.196884 0.023 Uiso calc 1 . .
C C8 0.9874(3) 0.7069(5) 0.57894(11) 0.0160(6) Uani d 1 . .
C C13 0.4584(3) 0.7580(5) 0.28265(11) 0.0151(6) Uani d 1 . .
C C9 1.0722(3) 0.8197(6) 0.60178(11) 0.0202(6) Uani d 1 . .
H H9 1.139(2) 0.900(5) 0.6217(11) 0.027(9) Uiso d 1 . .
H H1 0.605(3) -0.294(4) 0.6351(12) 0.028(9) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C13 N2 C10 . . 112.9(2) ?
C13 N2 I1 . . 123.98(17) ?
C10 N2 I1 . . 123.08(16) ?
C4 N1 C5 . . 119.0(2) ?
C1 C2 C3 . . 177.1(3) ?
O1 C10 N2 . . 124.3(2) ?
O1 C10 C11 . . 127.5(2) ?
N2 C10 C11 . . 108.2(2) ?
N1 C4 C3 . . 122.5(2) ?
N1 C4 H4 . . 118.8 ?
C3 C4 H4 . . 118.8 ?
C10 C11 C12 . . 105.0(2) ?
C10 C11 H11A . . 110.8 ?
C12 C11 H11A . . 110.8 ?
C10 C11 H11B . . 110.8 ?
C12 C11 H11B . . 110.8 ?
H11A C11 H11B . . 108.8 ?
C5 C6 C7 . . 118.2(2) ?
C5 C6 C8 . . 120.7(2) ?
C7 C6 C8 . . 121.1(2) ?
N1 C5 C6 . . 122.8(2) ?
N1 C5 H5 . . 118.6 ?
C6 C5 H5 . . 118.6 ?
C6 C7 C3 . . 119.6(2) ?
C6 C7 H7 . . 120.2 ?
C3 C7 H7 . . 120.2 ?
C4 C3 C7 . . 117.9(2) ?
C4 C3 C2 . . 121.9(2) ?
C7 C3 C2 . . 120.2(2) ?
C2 C1 H1 . . 179(2) ?
C13 C12 C11 . . 105.0(2) ?
C13 C12 H12A . . 110.8 ?
C11 C12 H12A . . 110.8 ?
C13 C12 H12B . . 110.8 ?
C11 C12 H12B . . 110.8 ?
H12A C12 H12B . . 108.8 ?
C9 C8 C6 . . 176.3(3) ?
O2 C13 N2 . . 124.2(2) ?
O2 C13 C12 . . 127.1(2) ?
N2 C13 C12 . . 108.7(2) ?
C8 C9 H9 . . 176.1(19) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
I1 N2 . 2.092(2) ?
O1 C10 . 1.209(3) ?
O2 C13 . 1.217(3) ?
N2 C13 . 1.382(3) ?
N2 C10 . 1.393(3) ?
N1 C4 . 1.337(3) ?
N1 C5 . 1.339(3) ?
C2 C1 . 1.180(4) ?
C2 C3 . 1.436(4) ?
C10 C11 . 1.511(3) ?
C4 C3 . 1.396(3) ?
C4 H4 . 0.9500 ?
C11 C12 . 1.531(4) ?
C11 H11A . 0.9900 ?
C11 H11B . 0.9900 ?
C6 C5 . 1.387(3) ?
C6 C7 . 1.388(4) ?
C6 C8 . 1.441(4) ?
C5 H5 . 0.9500 ?
C7 C3 . 1.398(4) ?
C7 H7 . 0.9500 ?
C1 H1 . 0.936(17) ?
C12 C13 . 1.507(4) ?
C12 H12A . 0.9900 ?
C12 H12B . 0.9900 ?
C8 C9 . 1.184(4) ?
C9 H9 . 0.932(17) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C11 H11A I1 2_655 0.99 3.35 4.219(3) 147.1 yes
C11 H11A O1 2_645 0.99 2.89 3.388(3) 112.3 yes
C11 H11B O1 2_655 0.99 2.95 3.474(3) 114.0 yes
C11 H11B O2 1_565 0.99 2.87 3.646(3) 135.9 yes
C12 H12A O2 2 0.99 2.72 3.545(3) 141.4 yes

_cod_database_fobs_code 2022627
